chemistry of carbohydrates - srm · pdf filereducing properties. z. oxidation. z. reduction....
TRANSCRIPT
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CHEMISTRY OF CARBOHYDRATES
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DEFINITION
Carbohydrates are polyhydroxy aldehydes or ketones or compounds which yield these on hydrolysis.
C
C O HH
C HH O
C O HH
C O HH
C H 2 O H
D -g lu c o s e
OH
C HH O
C O HH
C O HH
C H 2 O H
C H 2 O H
C O
D -f r u c to s e
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BIOMEDICAL IMPORTANCE
1. Most abundant dietary source of energy.2. Also serve as storage form of energy –
Glycogen.3. Participate in the structure of cell membrane
& cellular functions (cell growth, adhesion and fertilization).
4. Mucopolysaccharides form the ground substance of mesenchymal tissues.
5. Certain carbohydrate derivatives are used as drugs, like cardiac glycosides / antibiotics.
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ASSOCIATED DISORDERS
Derangement in Glucose metabolism –Diabetes Mellitus.Inherited deficiency of certain enzymes in metabolic pathways of different carbohydrates cause diseases.
• Glycogen storage disorders• Galactosemia• Hereditary fructose intolerence• Lactose intolerance, etc.
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SOURCES
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CLASSIFICATION
Based on number of sugar units present.Monosaccharides.
Cannot be hydrolyzed further into simpler forms.Disaccharides.
Yield 2 molecules of same or different monosaccharide units on hydrolysis.
Oligosaccharides.Yield 3-10 molecules of monosaccharide units on hydrolysis.
Polysaccharides. Yield more than 10 molecules of same or different monosaccharide units on hydrolysis.Homo- & Heteropolysaccharides.
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MONOSACCHARIDES
Simplest group of carbohydrates, cannot be further hydrolysed.
General formula : Cn(H2O)n
Categorization of monosaccharides is based onthe Functional Group. (Aldehyde or keto)the Number of Carbon atoms.
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MONOSACCHARIDES BASED ON FUNCTIONAL GROUP
ALDOSEKETOSE
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COMMON MONOSACCHARIDES
No. of C atoms
Generic name Aldoses Ketoses
3 Triose Glyceraldehyde Dihydroxy acetone
4 Tetrose Erythrose Erythrulose
5 Pentose RiboseXylose
RiluloseXylulose
6 Hexose GlucoseGalactose
Fructose
7 Heptose Glucoheptose Sedoheptulose
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STEREOISOMERS
Compounds having same structural formula, but differ in spatial configuration.Asymmetric Carbon atom: Attached to four different atoms or groups.Vant Hoff’s rule: The possible isomers (2n) of a given compound is determined by the number of asymmetric carbon atoms (n).Reference C atom: Penultimate C atom, around which mirror images are formed.
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GLYCERALDEHYDE STEREOISOMERS
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D & L ISOMERISM OF GLUCOSE
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OPTICAL ACTIVITY
Dextrorotatory (+) : If the sugar solution turns the plane of polarized light to right.
Levorotatory (–) : If the sugar solution turns the plane of polarized light to left.
Racemic mixture: Equimolar mixture of optical isomers has no net rotation.
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EPIMERISM
Sugars are different from one another, only in configuration with regard to a single C atom (other than the reference C atom).
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MUTAROTATION & ANOMERISM
When D-glucose is crystallised at room temp. and a fresh solution is prepared, its specific rotation of polarised light is + 112.2O;but after 12-18 hrs it changes to + 52.50. If initial crystallisation takes place at 980 C, initial rotation is +190, which also changes to 52.50.
Anomers are produced by spatial configuration with reference to 1st C atom in aldoses and 2nd C atom in ketoses.
So, total 32 isomers are there for glucose.
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α AND ß ANOMERS OF D-GLUCOSE
H O
OH
H
OHH
OH
CH2OH
H
OH
H H O
OH
H
OHH
OH
CH2OH
H
H
OH
α-D-glucose β-D-glucose
23
4
5
6
1 1
6
5
4
3 2
H
CHO
C OH
C HHO
C OHH
C OHH
CH2OH
1
5
2
3
4
6
D-glucose (linear form)
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DIFFERENT REPRESENTATIONS OF GLUCOSE STRUCTURE
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6
FISCHER’S FORMULAHAWORTH FORMULA
OPEN CHAIN PROJECTION
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GLUCOSE VS. FRUCTOSE
β D glucopyranose is the stable form of glucose and it exhibits the dextro rotation.
Fructose exits as β D furanose & exhibits laevo rotation.
β D glucopyranose β D fructofuranose
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REACTIONS OF MONOSACCHARIDES
Tautomerization or Enolization.
Reducing properties.
Oxidation.
Reduction.
Dehydration.
Formation of Esters
Glycoside formation.
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ENEDIOL FORMATION
In mild alkaline solutions, carbohydrates containing free sugar group tautomerises to form enediols, where 2 –OH groups are attached to double-bonded carbon.
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REDUCING PROPERTIES
Attributed to the free aldehyde or keto group of anomeric carbon.
Tests done to identify the reducing action of sugars include :
Benedict’s test.Barfoed’s test.Fehling’s test.Osazone test.
Reduction is more efficient in alkaline medium than in acidic medium.
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SUGAR ENEDIOL
SUGAR ACID
Cu++ CuSO4
Cu+
2Cu(OH)2Cu2O
OXIDISED REDUCED
BENEDICT’S TEST: PRINCIPLE
REAGENT: Na2CO3, CuSO4, Na citrate
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BENEDICT’S TEST
water 0.5-1% 1- 1.5% 1.5– 2%
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BARFOED’S TEST
Reducing monosaccharides are oxidized by the copper ion in solution to form a carboxylic acid and a reddish precipitate of cuprous oxide within three minutes.
Red scum at bottom
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FEHLING’S TEST
Fehling I:CuSO4
Fehling II: K-Na- tartrate + NaOHFehling's reagent: Equal volumes of Fehling I and Fehling II are mixed to form a deep blue solution.
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OSAZONE FORMATION
Phenylhydrazine in acetic acid, when boiled with reducing sugars, forms osazones.
FRUCTOSEPHENYL
HYDRAZINE FRUCTOSAZONE
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GLUCOSAZONE:NEEDLE SHAPED
LACTOSAZONE: HEDGEHOG SHAPED MALTOSAZONE: SUNFLOWER
SHAPED
OSAZONE CRYSTALS
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OXIDATION
C
C OHH
C HHO
C OHH
C OHH
CH2OH
D-glucose
OH
Gluconic acid
Glucuronic acid
Glucosaccharic acid
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REDUCTION
C
C OHH
C HHO
C OHH
C OHH
CH2OH
D-glucose
OH
C HH O
C O HH
C O HH
CH 2O H
CH 2O H
C O
D -fructose
D-
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Furfurals condense with phenolic compounds (α-naphthol) to form coloured products.
Basis of the “Molisch test”.
12
345
6
Conc. H2SO4
3H2O
DEHYDRATION
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FORMATION OF ESTERS
Esterification of alcoholic groups of mono-saccharides with phosphoric acid is a common reaction in metabolism.
Examples :Glucose-6-phosphate, and Glucose-1-phosphate.
ATP donates the phosphate moiety.
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GLYCOSIDE FORMATION
The hydroxyl group of anomeric carbon of a carbohydrate can join with a hydroxyl group of another carbohydrate or some other compound to form a glycoside and the bond so formed is known as glycosidic bond.eg. R-OH + HO-R' R-O-R' + H2O
The non-carbohydrate moiety is known as aglycone –phenol, sterol, bases, CH3OH, glycerol.
Glycosidic bond can be N-linked or, O-linked.
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N-Glycosidic linkage O- Glycosidic linkage
N & O GLYCOSIDIC LINKAGE
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BIOMEDICAL IMPORTANCE OF GLYCOSIDES
Cardiac Glycosides – Digoxin, DigitoxinUsed in cardiac insufficiency.Contain steroids as aglycone component.
Ouabain – Sodium pump inhibitor.Streptomycin – AntibioticPhloridzin – cause renal damage, glycosuria.
Obtained from root & bark of apple tree.Blocks the transport of sugar across the mucosal cells of small intestine & also renal tubular epithelium.
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AMINO SUGARS
Amino groups are substituted for hydroxy groups of sugars.
H O
OH
H
OH
H
NH2H
OH
CH2OH
H
α-D-glucosamine
H O
OH
H
OH
H
NH
OH
CH2OH
H
α-D-N-acetylglucosamine
C CH3
O
H
NH O
H
COO−
OH
H
HOH
H
H
RCH3C
O
HC
HC
CH2OH
OH
OH
N-acetylneuraminate (sialic acid)
R =
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DEOXY SUGARS
Oxygen of the hydroxyl group is removed to form deoxy sugars.Non reducing and non osazone forming.Important part of nucleic acids.
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DISACCHARIDES
Two monosaccharides combined together by glycosidic linkage.
Reducing : Maltose, Lactose – with free aldehyde or keto group.
Non-reducing : Sucrose, Trehalose – no free aldehyde or keto group.
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SUCROSE
Cane sugar.
α-D-glucose & β-D-fructose units held together by (α1→ β2) glycosidic bond.
Reducing groups in both are involved in bond formation, hence non reducing.
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INVERT SUGAR
Sucrose is dextrorotatory. (+66.50)
During hydrolysis, sucrose is first split into α-D-glucopyranose & β-D-fructofuranose (both dextrorotatory).
β-D-fructofuranose is less stable and immediately converted to β-D-fructopyranose (strongly levorotatory).Net rotation : – 28.20.
Sweeter than sucrose.
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LACTOSE
Present in milk.
β-D-galactose & β-D-glucose units held together by β (1→4) glycosidic bond.
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MALTOSE
Malt sugar.Produced during the course of digestion of starch by the enzyme amylase.
Two α-D-glucose units held together by α (1→4) glycosidic bond.
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POLYSACCHARIDE
Repeat units of monosaccharides or their derivatives held together by glycosidic bonds.
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HOMOPOLYSACCHARIDES
Starch
Glycogen
Cellulose
Inulin
Dextrans
Chitin
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STARCH
Carbohydrate reserve of plants. Present in Cereals, Roots, Tuber, Vegetables.
Consists of Amylose (water soluble) & Amylopectin (water insoluble).
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AMYLOSE
Long unbranched chain.
200 – 20,000 D-glucose units held together by α (1→4) glycosidic linkages.
AMYLOSE
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AMYLOPECTIN
Branched chain. (α 1→6 glycosidic bonds at branches).
20 – 30 glucose units per branch.
AMYLOPECTIN
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HYDROLYSIS OF STARCH
Colour disappears with heating and reappears when cooled.Starch is non reducing.Hydrolysis for a short time: Violet colour due to Amylopectin (non reducing).Further hydrolysis: Red colour due to Erythrodextrin (reducing).Later Achrodextrin & Maltose (both reducing).
+ve -ve
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ACTION OF AMYLASE
Starch Dextrins α/ß-Maltose
Amylopectin
Maltoses
Salivary & pancreatic α-amylase or ß-
amylase
ß-amylase Limit dextrin
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GLYCOGEN
Reserve carbohydrate in animals. Stored in liver & muscle.Forms red-brown/brown-violet colour with iodine.Contains primer protein: Glycogenin.More branched and compact than amylopectin. Every 11th sugar molecule has a branch.
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GLYCOGEN STRUCTURE
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CELLULOSE
Chief carbohydrate in plants.Made up of glucose units combined with cellobiose bridges.No branching point.Cannot be digested by human due to absence of Cellobiase.
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INULIN
Inulin is made up of D-fructose units with repeating ß-1,2 linkages.
It acts as a marker for glomerular filtration since it is not synthesized, metabolized but filtered completely by glomerulus.
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CHITIN
Chitin is found in crustaceans eg.lobsters,crabs,shrimps,insects.
Composed of N-acetyl glucosamine units joined by ß-1,4 glycosidic linkages.
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HETEROPOLYSACCHARIDES
Agar
Mucopolysaccharides:
Hyaluronic acidHeparinChondroitin sulphateKeratan sulphateDermatan sulphate
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AGAR
Prepared from sea weeds.Contains Galactose, Glucose and other sugars.Used as supporting medium for immunodiffusion & immunoelectrophoresis.Agarose contains Galactose combined with3,6 anhydrogalactose units.Agarose is used as matrix for electrophoresis.
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MUCOPOLYSACCHARIDES
Also known as GAG.Made up of repeating units of sugar derivatives (aminosugars and uronic acids). Acetylated amino groups, sulfates and carboxyl groups are generally present.
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HYALURONIC ACID
Present in connective tissues, tendons, synovial fluid and vitreous humor.Composed of repeating units of N-acetyl glucosamine → ß-1,4 glucuronic acid → ß-1,3 N-acetyl glucosamine.
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HEPARIN
Anticoagulant. Bind and activate Antithrombin III, which in turn activates Thrombin, Factor X & Factor IX.Present in lung, spleen and monocytes.Contains repeating units of sulphated glucosamine → α-1,4 L-iduronic acid.Sulphated: Heparan sulphate
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CHONDROITIN SULPHATE
Present in ground substances of connective tissues of cartilages, bones & tendons.Composed of Glucuronic acid → ß-1,3 N-acetyl galactosamine sulphate → ß-1,4 and so on.
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KERATAN SULPHATE
Only GAG not having Uronic acid.Found in cornea and tendons.Repeating units are Galactose & N-acetyl galactosamine in ß linkage.
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DERMATAN SULPHATE
Found in skin, blood vessels & heart vessels.Contains L-iduronic acidand N-acetyl galactosamine in ß-1,3 linkage.
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MUCOPLYSACCHARIDOSIS
NAME ENZYME DEFECT URINARY METABOLITES
MPS I : Hurler’s α -L-Iduronidase Dermatan sulfate Heparan sulfate
MPS II: Hunter’s Iduronate sulphatase Dermatan sulfateHeparan sulphate
MPS IIIA: San Filippo AMPS IIIB: San Filippo BMPS IIIC: San Filippo CMPS IIID: San Filippo D
Sulfamidaseα-N-acetyl glucosaminidaseAcetyl transferaseN-acetyl glucosamine 6 sulfatase
Heparan sulfate Heparan sulfateHeparan sulfateHeparan sulfate
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MUCOPLYSACCHARIDOSIS
NAME ENZYME DEFECT URINARY METABOLITES
MPS IVA: Morquio AMPS IVB: Morquio B
Galactosamine 6 sulfataseß-galactosidase
Keratan sulfate, Chondroitin 6-sulfate
MPS VI: Maroteaux-Lamy
Arylsulfatase B Keratan sulfate
MPS VII: Sly ß-glucuronidase Dermatanan sulphate
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PROTEOGLYCANS & GLYCOPROTEINS
Proteoglycans: When carbohydrate chains are attached to a polypeptide chain.Glycoproteins: Carbohydrate content ≤ 10%.Mucoprotein: Carbohydrate content ≥10%
Proteoglycan
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